Jeff and Annie's First Five Christmas's
by robert3A-SN
Summary: A look at how Jeff and Annie give each other Christmas presents from Christmas 2009 to 2013, as their gifts get progressively more sweeter, thoughtful and romantic over time – even from Jeff.


**Christmas 2009**

Jeff was fairly new to having real friends, let alone getting them Christmas presents. He got gifts for people at the firm, but that was just to suck up to them or to make them owe him favors later. So buying heartfelt gifts for people he was starting to….do more than tolerate, wasn't something he mastered the first time out.

Jeff just took the basic things he knew about everyone and got quick, generic presents from that without a second thought. He didn't exactly have much money for more expensive gifts, so that made a difference too. That's why he only got a cross for Shirley, a football for Troy, a Darth Vader figurine for Abed, a cat food bowl for Britta, and a wig for Pierce like the one he wore on Halloween.

For Annie, Jeff knew she loved to write notes and wore purple a lot. So he combined those and got her a collection of purple pens. Some people might think it was cheap and not too Christmas-y. But even those who'd appreciate it anyway might not have jumped up and hugged Jeff like Annie did, when presents were exchanged on the last day of the semester in the study room.

"Jeff, this is perfect!" Annie cheered when she was done squeezing him. "These'll be great for my notes next semester! And there's enough for you guys to borrow and write some notes yourself!"

"Right, I'm sure we can do some of those things," Britta dodged.

"And if not, they'll be easy for us to find in a pinch, so win win," Jeff said with unknowing irony.

Annie kept bouncing, even as she went over and got Jeff his present. She only handed him an envelope, so Jeff's expectations didn't soar right away. Then he opened it, took out the four pieces of paper inside and just studied them for a while. "What's this?" he finally asked?

"I thought it was obvious, Jeff. They're gift certificates. To all your favorite salons where you get hair and face care stuff," Annie explained.

Jeff still didn't have a comment, so Annie continued for him. "Look, you talk about their products all the time. And you're kind of right to brag, to a point. And I know you'll go to these stores over break, just in case your bruises don't fade fast enough," she noted while pointing to Jeff's still prominent bruises from the recent Christmas brawl.

"And I know you're still short on money right now. Even after buying these gifts. So maybe with my gifts, you won't spend the rest of it on products, you'll still afford your other cool stuff, and you'll look perfect in public again after the break. You still look good enough now, but I know you can't just take our word for it, so…." Annie trailed off a little shyly.

Jeff didn't jump up and down like Annie did over her present. Yet the fact that he was stunned – and _quiet_ – was the best endorsement to how much this floored him. But he tried to be vocal about it anyway and got out a, "Thanks…." Then to salvage his image, he added, "I mean, helping me look good is a gift to all of us. So it really counts as a group present."

That brought out the expected groans, Britta complaints and eventual Troy and Abed gimmicks. But Annie just smiled and nodded to acknowledge Jeff's thank-you. Which made him feel….odd about not saying more.

Of course, if he said more, he'd have had to acknowledge that no one ever put that much thought into a Christmas present for him. That while it was predictable for Annie to be so thorough, it was still something that she was so….observant. To notice he had a hard time with not looking perfect right now, and worried about paying for perfection again.

And instead of just mocking him and joking about it, she tried to help him. She cared and thought enough about him to really help him. And it would probably work, too.

Having actual friends was one thing. Having someone…._know _Jeff like Annie seemed to sometimes was quite another. And from someone who once kissed him at that. No one he'd ever kissed had gone to that much trouble for him. At least not the kind that didn't drive him crazy or make him run for the hills by now.

Then again, he'd only known Annie and all these people for four months. By the time these nightmarish four years ended, she and them would probably be a distant memory.

For the first time – or the first he was willing to notice – Jeff didn't feel 100 percent relieved about that.

**Christmas 2010**

Pretending to stay stop motion animated in Abed's dorm room didn't last the entire holiday season. But Annie was adjusted enough to live action again by the time everyone exchanged presents. The surest sign that they were back in reality was the very real nerves Annie felt about exchanging gifts with Jeff.

Predictably, they didn't bring up a certain lyric they sang together in "That's What Christmas Is For." Which included a certain "L" word that they sang and came up with out of the blue together. It wasn't just Annie making it up like the crazy school girl she was four months ago. She was getting better at acting better – even though Jeff couldn't be bothered to get better and admit that there was –

But there was no sense having a relapse now. Just in case, she made sure that she and Jeff would exchange gifts privately, with no spying from the group. When they finally got a moment to themselves, they just stood in the hall awkwardly until Jeff merely handed her a wrapped gift.

Maybe Jeff's actions would speak louder and get better results than his words. And when she unwrapped it and found three DVDs of her favorite stop-motion Christmas movies, it was off to a promising start.

"I know we've been watching this stuff for days. But I know you'd like to watch it again at home, whether we're around or not," Jeff explained. "Now you won't need to rent these from Abed for the whole break, so…."

Annie didn't have the heart to tell him she already owned two of these movies. Having the third one was good enough, and having new copies of the other two from Jeff was even better. He clearly put real thought and spent a lot on this just for her. More and more she realized how rare, and therefore special, that was from him.

Besides, he couldn't know she already had some of these movies – it's not like he'd ever been to her rotten apartment to check. Or even knew where it was….thankfully.

"Jeff, I love these. Thank you," she exclaimed, without managing to jump up and hug him. That would probably do more harm than good – plus her hands were too full now anyway. Well, she could at least make one hand free by handing over her present.

But first, she had to make something clear to him. "Jeff, before I give you this, you have to promise not to tell anyone about it. Especially the Dean."

"Well, this is already one of my top five gifts of all time," Jeff quipped. "Care to squeeze into the top three?" he asked while reaching out for the present.

"Jeff, I'm serious," Annie stressed again. "I wanted to help the Dean out after our conspiracy mess. So I offered to help him edit his time-travel book."

"You….you _saw _Dean Dangerous?" Jeff tried to comprehend.

"He only showed me the first five chapters. It's….about what you'd expect," Annie said, trying to be as nice as possible. "But I edited it into something that….might be salvageable! I even made copies of the original draft, so we could go over what _not _to do!" She then paused and offered, "And if you _promise _never to say _anything _to the Dean, even a little joke….I'll let you have one of the copies."

Jeff took Annie's package and studied it, but she further warned, "But you put it in the car _right now_, don't let the others see it and keep it in your apartment, okay? I won't feel _that _much guiltier if I can't see or hear –"

Annie could only hear her own heartbeat after Jeff interrupted her with a big hug. Her eyes couldn't stay still either, as she looked around to see if anyone was there – or just tried to focus on something other than Jeff.

"Annie, you are the best gift-giver ever," Jeff declared right before breaking off. "Tell them I'm charging my phone, I won't come out for several hours, stuff like that!" he called out as he ran and ripped through the wrapping paper all at once.

Well, he did say she was a great gift-giver. It wasn't a real declaration of how he felt for her, if he felt anything at all. It just praised her for a skill, not for Annie herself. Not that Annie was looking for that, or should have been looking for it, or….should even want to look for it.

Even when they exchanged sweet, ultra personal, kind of Dean-betraying presents, there was way too much ambiguity between them now. Of course, Jeff was just excited to trash the Dean's trashy writing – although it was slightly less trashy in Annie's version.

She was left to pick up the pieces, wonder over things he couldn't be bothered to think about, and look like a crazy, deluded little girl for even daring to think that way. Whereas he could be oblivious and thoughtless and it was regarded as a-ok!

Annie finally sighed and tried to drop it. It was less and less worth it to think that way, especially when it threatened Christmas cheer. Maybe resolving to stop doing this, take a hint from Jeff – and maybe enjoy time with other guys a bit more – was a good thing to resolve for New Years.

But for now, she'd just have to pick up the wrapping paper, destroy that evidence, and keep trying to hang around Jeff and the Dean with a straight face next year.

**Christmas 2011**

Jeff looked around for the 15'th time to see if anyone saw him at the Troanniebed door. Maybe he'd actually knock after a 16'th check.

But Jeff already covered his tracks well. He bought his Christmas gift for Annie and wore a hat and shades so no one would recognize him. He waited until Troy and Abed left the apartment, waited a good 20 minutes to actually go in the building, and waited 15 minutes to actually go up to Annie's floor.

Maybe another five minutes would be enough. Then again, he'd already tempted fate too much by standing here this long. If he just knocked on the door now and got inside fast enough, maybe only Annie would see him in…..her Christmas present.

So after knocking on the door and enduring the longest 10 seconds of his life, Annie finally opened up. Jeff barely gave her time to gawk at him before running inside and locking the door. At last, he was safe. Safe for Annie to see him dressed up in a _Santa suit_.

"Ho ho ho, ho ho ho!" Jeff said to sell it further. "I wear silly red suits too! Ho ho ho!"

"Jeff….what the hell?" was all the otherwise speechless Annie could ask.

"It's simple, young lady!" Jeff talked behind his _extremely _unflattering fake white beard. "You were brainwashed to dress and act like a baby Santa, and you've been uncomfortable around one of your friends ever since! So now he's dressing as a silly, very _unsexy _Santa to make you even! And thus, all awkwardness and weirdness between you two is gone! It's a Christmas miracle!"

"But….but…." Annie repeated before getting a hold of herself. "You're dressed like a regular Santa. You're not halfway nude, or singing, or talking like a baby or anything."

"Look, your friend is hiding his gorgeous face and suits. And he risked people seeing him like this in _public_. That's more embarrassing than a sexy brainwashed Santa any day! So now you and him are even, simple as that!" Jeff declared, still too humiliated to talk in the first person in this outfit.

Annie kept gawking in silence, but soon let out a little chuckle. "So you – I mean Jeff – tried to make us even. Like he did with Britta and those drunk calls that Valentine's Day? Only with Santa suits?" she asked while hiding more chuckles.

"Well, he's not one to ignore a winning formula. So, you're even? He can go now?" Jeff tried to wiggle out of it early. But he was still around as Annie laughed longer and louder. Somehow, Jeff didn't beat a retreat then and there, and waited for Annie to use her words again.

"Jeff, this is so….stupid and so sweet all at once," Annie conceded.

"So, that's good? Like, now we're even and all good, good?" Jeff checked.

Annie caught her breath and answered, "Jeff, you actually _noticed _I was….uncomfortable?" When Jeff stayed still and answered her that way, Annie looked less happy than she was minutes ago. "Well, it wasn't because of you or us. It's me and how _un_sexy I really was."

"Annie, I put on a Christmas _sweater_ because of that performance. And that isn't even the worst thing I wore this holiday season, as it turns out!" Jeff pointed out while pointing to his current attire. "Trust me, diminishing returns or not, it was sexy enough! Besides, it was Glee's fault anyway!"

"Glee isn't why I don't know how to be sexy!" Annie let out. "I just….I don't know how to be sexual or romantic like a grown up! I go boy crazy at the drop of a hat, I romanticize every little moment, and I see things that aren't there! And now I seduce people like babies, apparently!"

She slumped down on Abed's recliner and finished, "I'm just too awkward and uptight and….childish to express my sexuality. At least in the grown up, sexy way. No matter what time of year it is. I guess being around you made me too sensitive to that right now. But it won't be so bad after the holidays, so…"

Jeff tried not to dwell on how he played some role in Annie forming this theory, but it was hard. His best idea to distract himself was to blurt out, "Come on, Annie, you're plenty sexy!"

Before Jeff could backtrack, Annie answered, "Yeah, for someone who wears frumpy cardigans all the time. And ruins sexy outfits by talking wrong."

"Annie, you could wear the ugliest cardigans ever and still be hot. And you have!" Jeff let out without thinking. But not thinking would have to do right now.

Otherwise, he might think no matter how her body was covered or not, her face was still more than beautiful enough to make her sexy – in ways he'd never thought of about a face before. In ways that shouldn't overshadow a body like hers, but they did. And that's why it was best not to think about it.

But Jeff owed her something more, so he settled for, "Annie, you're not sexy as a baby, we've established that. But the real you? The regular Annie? Well, that's plenty hot enough."

"For who?" Annie inquired, which left Jeff on dangerous ground. Yet there was a way to dance around this while still making her feel better.

"For anyone," Jeff answered and hoped it was good enough.

"Well, maybe on looks, anyway. But the way I act sometimes….and the way I act when I'm _not _a baby," Annie reflected. "That's not most people's idea of sexy."

"You're right," Jeff suddenly started, "I mean, I wouldn't have found your quirks hot four years ago. Being sweet, smart, caring, thoughtful…..someone who wants to be good and do good for_ selfless_ reasons….someone who'll stick by giant jackasses when they don't deserve it….these aren't things I considered sexy back then. But now…..I mean, when _you _do it…"

Jeff stumbled before settling on a good closer. "Annie, being all of those things, just being the real _you_….that's sexy enough by any standard. Enough that the baby stuff and clingy stuff doesn't matter. Or shouldn't matter, anyway. Anyone with a brain should see that, so _you _should know it better than anyone. Okay?"

Jeff had no idea how he went that far, or how much he'd screwed himself by being that….truthful. But just as he started to get really nervous, Annie smiled a bit and seemed to settle his stomach down. Why did her smiles keep doing that?

"You're really getting better at gift-giving, Jeff," Annie admitted. It didn't tell Jeff whether she was okay, or believed him, or had any more suspicions about what he said. Instead, she suddenly lit up and exclaimed, "You know, now I think _your _Christmas gift should come early too."

Annie sprung up and went into the closet, as Jeff was amazed at how quickly her mood changed. As if nothing had happened minutes earlier, she seemed to be in full on Christmas spirit mode as she came back with a big, wrapped box. This looked promising in a few ways.

Annie handed it over with just a smile, so Jeff put it on the living room table and started unwrapping. He then opened the exposed box and almost literally gasped. "Is that…."

"Uh huh. You raved about seeing that suit weeks ago. That gave me just enough time to save up for it," Annie filled in. "At least now you don't have to leave in….that other suit after all."

Jeff had actually forgotten about his unflattering Santa suit. Technically, he forgot ever since Annie's sexiness became a debate topic. Now he was too busy drooling over this perfect, formerly too expensive for him suit. He didn't even dare to take it out of the box yet, for fear of disturbing the fabric.

"Annie, this…." Jeff exclaimed, now out of big speeches. "I….well, my gift-giving isn't _that _improved by comparison."

"You're welcome, Jeff," Annie said, in perhaps more than one way. "Maybe you can wear it when you find a new shrink. To give you confidence and all."

Jeff was now speechless for less uplifting reasons, but Annie acted quickly. "Jeff, it's okay. I know you've had a rough time lately. But anyone who could do and say the things you've done for us….today and otherwise," she left hanging.

Yet she picked back up and finished, "You just find someone who can do as much for you as you do for us. And don't give him the wrong idea about you. No matter what you wear or what you've done, you're so much better than you give yourself credit for. Trust me. And trust me when I say you're finally gonna be fine."

"What did you just say?" Jeff gasped out.

"You're gonna finally be fine," Annie said simply, apparently unaware of what she had said. Hopefully she was unaware. As long as he didn't talk or sing in his sleep four months ago, then….

"Would you be fine changing into that suit now?" Annie sensed. "I've got some extra closet room for your other suit now. Just so you know."

"Huh? Oh right, hide the evidence, got it, thanks," Jeff blurted, then awkwardly took the Santa suit off and avoided looking at Annie. He cursed himself a little for letting it end like that, although he had drained his strategic sentiment reserves minutes ago. Probably for the best that it was all dry right now….probably.

But getting that suit on at long last would make it even better. Regardless of whether Annie saw him change or not. Still, no need to make her drool like a baby for a _good _reason. Probably.

**Christmas 2012**

Annie knew the drill by now. She and Jeff found a private place in her apartment building, to exchange Christmas gifts without the group bugging them. Jeff insisted on it more, but that wasn't a surprise. Whatever that meant, and for whatever reason he wanted to hide this from the group, Annie figured it was best not to analyze it. Even though Britta probably already knew.

Yet it wasn't the time to think about that. This was their last Christmas together as Greendale students, and Annie had to have fun now – at least before she had to resume studying for her new major. So it was best to just exchange gifts, although Annie feared this wouldn't live up to past standards.

Nevertheless, she handed Jeff the briefcase she was holding. "You couldn't have just wrapped my gift in paper, eh? Always have to do things the hard way," Jeff commented, with a tinge of an odd, strained tone in his voice.

"There's nothing in the briefcase, Jeff," Annie corrected. "You're holding your gift right now."

Jeff lifted up the briefcase, took a close look, then opened it to see there was nothing inside. This gave Annie as good an opening as any to further explain the gift.

"This is supposed to be your new legal briefcase. When you become a lawyer again. I wanted to engrave 'Property of Jeff Winger, Attorney' inside, but I'd spent too much by then! But I promise I'll get that written as soon as I can!" Annie assured.

Jeff stayed quiet, which was usually a good sign when it came to Christmas gifts, at the least. He ultimately added, "I do still have a briefcase from the old days, you know."

"That was in the past! When you faked your way into court, didn't have friends and didn't face your father once and for all. This is gonna be a better briefcase. For your better future," Annie confidently stated.

Jeff still stayed quiet, which was probably more of a bad sign by now. Finally, instead of saying thanks or giving her a hug, he reached in his pocket and pulled out an envelope. Annie took it and studied it, then prepared to open it before Jeff spoke up at last.

"Wait! You need to open it with your first gift!" he informed. He went back into his pocket and pulled out a new purple pen.

"Jeff! Thank you!" Annie squealed, hoping she wouldn't lose or never get back _this_ purple pen, unlike the last ones Jeff gave her. But even when she'd bought another purple pen herself to protect the other ones, it got stolen by Annie's Boobs, so it probably wouldn't matter either way. At the least, she kept this one long enough to open the envelope and take out her second gift.

At first glance, the piece of paper she took out looked to be a gift certificate. But it was one that Jeff made himself. And it wrote, "Good for 100 percent off of a dinner date with Jeff Winger. Redeemable at any time. Especially during holiday break."

Now it was Annie's turn to be speechless. In fact, she wasn't sure she'd speak again for the rest of 2012.

But she did force out, "You….you gave me pens and certificates. What are you, Abed with these callbacks?"

"Abed isn't asking you out. Thank God," Jeff got out with equal strain.

Annie tried to get her head straight, remembering the right way to deal with this now. "Jeff….what am I supposed to say to this?" she wondered, without assuming anything or getting all gooey.

"I was looking for one specific answer," Jeff answered back.

"Why?" Annie pleaded for honesty. "I thought you were into Britta again….and you and your dad…..and your last semester.…" She got herself back under control and coherently finished, "This is just you acting out because of one of those things. You're not thinking clearly….you _can't _be. I know what that's like, so I _know_."

"Annie, all that _finally _made me think clearly," Jeff corrected. "I wasted too much time before I dealt with him. And before I resolved things with her for good. Now I _can't _spend one more semester putting things off with you. Especially our _last _one."

"But I….you know I'm proud of you, but I…." Annie stammered. "Jeff, I don't know if I still….or if I even _should_," she finished as best she could.

"I know," Jeff sighed. "You don't need to answer right now. Take as long as you want, and if you need to talk to me, I promise I'll be….at least 75 percent honest." He chuckled a little, before once again looking more serious than Annie had ever seen him.

"There's no deadline, although I'd like to do it during break. Then whatever happens….we can know what we really are _before _we start saying goodbye to Greendale. I'd like to do it that way, and I think you would too." The whole notion of what Annie wanted or didn't want was the problem, however.

But she made herself ask, "And if it goes well….would it make us something you _want _to be?" She cursed herself for not being clear to him – as ironic as that was – and cleared up, "Jeff, do you want us to date? And then _keep _dating?"

Jeff didn't have an answer, which made Annie wish she was more surprised. At least he backed off before she could have started to get her hopes up. However, he then took her new certificate and took her new pen to write something on the back.

When he returned the paper, Annie saw he had written the word "YES" with four underlines below it. "Like I said, no need to answer now," Jeff stated out loud before finally retreating.

Annie could only think that Jeff had gotten even better than her at Christmas gifts. It was the only thing she could let herself think.

She took about a week to sort the rest out. Then she cashed in her certificate just in time for New Years.

**Christmas 2013**

Jeff made extra sure that he and Annie wouldn't be disturbed when they exchanged Christmas gifts. It helped that they were exchanging gifts on Christmas Eve at Jeff's apartment, the group wouldn't meet at Troanniebrittabed until tomorrow, and it was easier to get alone time as an official couple. It had been for almost a year, so they were getting good at it.

Nevertheless, as Jeff sat on his couch, he couldn't wait to see how good Annie was with her latest gift. Even though he might have finally outdone her this time.

"Jeff?" he heard in a ridiculously soft, sweet voice. Then when Jeff looked over, he couldn't hear anything but his heart beat.

Annie emerged from his bedroom, in a completely different outfit than the one she wore going in. In fact, it was a full on, sexy elf costume. It was complete with green stockings, a red skirt, a green top that more than showed off her….sugar plums, a hat and the traditional elf ears. Her lips were cherry red, and as she strolled over to Jeff in a breathtaking strut, he could have sworn her hair smelled like candy canes.

She was a living, breathing Christmas vision. And when she sat down and cuddled up to him, he was surprised he didn't….grow three sizes right then and there.

"Santa's little helper made this gift for me," Annie kept cooing sweetly. "Well, technically I did. All those years doing costumes for Troy and Abed finally paid off. But anyway, do you like your gift?" Before Jeff could answer, she added, "I mean, this is technically a gift for both of us, so it's kind of a group present."

"The group will never….Hell, I never…." Jeff tried not to stammer so much. Yet it was hard not to. Annie was decked out in sexy Christmas garb again, but there was nothing baby-ish and brainwashed in this performance.

She was sexy as all hell, and yet despite acting as a character for him, this was all Annie through and through. The Annie who was already sexy, gorgeous, sweet and made Jeff the luckiest man alive – only with some extra cleavage and a sultrier voice for this special occasion.

Speaking of special occasions, there was no better one than now for Jeff's present. He couldn't believe he was interrupting sexy elf Annie for this, but perhaps his priorities really had changed.

Without a word, he found his gift and went back over to give it to Annie. It was a small box, which Jeff knew might be misleading to Annie. Yet after her initial gasp, she opened it and looked a little disappointed at first. But when she saw what was actually inside, she gasped again.

"Jeff…." Annie breathed as she took out the house key from the box. "Is this…?"

"Your first Christmas gift in _our _apartment? Well, it is that," Jeff announced. "I figured after dinner at your old house tomorrow, we'd start packing up and moving you in here."

"Jeff…." Annie repeated. "What about….what about…."

"Yes, I asked your roommates' permission first. No, you don't want to know what I did for them to keep them quiet. Especially Britta. You'd think getting to be the only girl in that place would be enough for her, but-" Yet Jeff didn't finish his rant before Annie jumped into his lap.

"I can't believe you did this," Annie breathed into his neck. "You're the best gift-giver ever…."

"I had to learn _something _from you, didn't I?" Jeff figured, deliberately underselling it. Then Annie showed some of what she learned from Jeff by kissing him hard and fast.

Apparently Annie didn't mind that her hopes were even higher at first. But Jeff wasn't that far gone yet. Regardless of the extra look he gave that engagement ring before he got the key made.

Well, maybe that settled things for next Christmas, at least.


End file.
